Acetone → HCID 11187850, compound

HRID 1247533Notes

Reaction equation

HRID 1247533 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][C:17]([CH:20]([CH2:22][OH:23])[OH:21])([OH:19])[CH3:18])[CH3:13])[CH3:8])[CH3:3].[CH3:24][C:25]([CH3:27])=O>C1(C)C(S(O)(=O)=O)=CC=CC=1>[CH3:24][C:25]1([CH3:27])[O:21][CH:20]([C:17]([OH:19])([CH2:16][CH2:15][CH2:14][CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH3:18])[CH2:22][O:23]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 30185253,7,11,15-Tetramethylhexadecane-1,2,3-triol

Product 1

HCID 11187850HCID 11187850, compound

Reagents, catalysts & solvents 1

HCID 69252-Methylbenzenesulfonic acidCatalyst

Procedure

One g of phytantriol (3.0 mmol) was refluxed using deanstock apparatus for 15 hr in 25 ml of acetone solution with toluene sulfonic acid as catalyst. After the completion of the reaction, the acetone solvent was removed under reduced pressure and the resultant was extracted with chloroform solution. The extract was washed with saturated sodium bicarbonate solution and was again washed with saline to obtain 0.3 g of (2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6,10,14-trimethyl-pentadecan-2-ol) of which 1- and 2-positions were protected, which is represented by the following formula (IV):

Workup

  1. customfor 15 hr
  2. customAfter the completion of the reaction
  3. customthe acetone solvent was removed under reduced pressure
  4. extractionthe resultant was extracted with chloroform solution
  5. washThe extract was washed with saturated sodium bicarbonate solution
  6. washwas again washed with saline

Sources & evidence

ORD record
ord-573f6b2ac8b343029178749076e2c1de
Source dataset
uspto-grants-2006_10
Patent number
US07129275B2

Reaction notes

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